3 years ago

N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C–H Hydrogen Bonding

N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C–H Hydrogen Bonding
Xin Li, Guo-Hui Yang, Ye-Ye Shen, Xiao-Song Xue, Yao Li, Jin-Pei Cheng
A series of novel N-tert-butyl sulfinyl squaramide receptors have been designed and synthesized. Their interactions with a range of inorganic anions were studied in solution by 1H NMR spectroscopy. This new type of squaramide displayed better anion-binding abilities over conventional diphenyl squaramides. The single crystal analysis and DFT calulations implied the role of the tert-butyl C–H protons in binding Cl. The energies of C–H···Cl interactions were estimated to be 1.4–1.6 kcal/mol in solution.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01634

DOI: 10.1021/acs.joc.7b01634

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